This invention relates to certain herbicidal sulfonamides, agriculturally suitable compositions thereof and a method for their use as a general or selective preemergent or postemergent herbicide or as a plant growth regulant.
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around fuel storage tanks, ammunition depots and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
The "sulfonylurea" herbicides are an extremely potent class of herbicides discovered within the last few years which generally consist of a sulfonylurea bridge, --SO.sub.2 NHCONH--, linking two aromatic or heteroaromatic rings.
U.S. Pat. No. 4,394,506 discloses herbicidal ortho-alkoxycarbonylbenzenesulfonamides such as ##STR1## wherein R.sub.2 is H, F, Cl, Br, C.sub.1 -C.sub.3 alkyl, NO.sub.2, SO.sub.2 CH.sub.3, OCH.sub.3, SCH.sub.3, CF.sub.3, N(CH.sub.3).sub.2, NH.sub.2 or CN;
X is H, Cl, CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3 or OCH.sub.2 CH.sub.2 OCH.sub.3 ; and PA0 Y is H, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 substituted alkyl, C.sub.1 -C.sub.4 alkoxy, etc. PA0 X is O, S, SO or SO.sub.2 ; PA0 R.sub.1 is H, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl or YR.sub.5 ; PA0 R.sub.2 is H, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl, C.sub.1 -C.sub.4 haloalkyl, CO.sub.2 R.sub.6, YR.sub.5, NO.sub.2 or CONR.sub.7 R.sub.8 ; and PA0 R.sub.3 and R.sub.4, each independently of the other, are hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, halogen or alkoxyalkyl of at most 4 carbon atoms. PA0 X is O, S, SO or SO.sub.2 ; PA0 R.sub.1 is H, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl or YR.sub.5 ; PA0 R.sub.2 is H, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl, C.sub.1 -C.sub.4 haloalkyl, CO.sub.2 R.sub.6, YR.sub.5, NO.sub.2 or CONR.sub.7 R.sub.8 ; and PA0 R.sub.3 and R.sub.4, independently of one another, are hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, halogen or alkoxyalkyl of at most 4 carbon atoms. PA0 X is O, S, SO or SO.sub.2 ; PA0 R.sub.1 is H, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl or YR.sub.5 ; PA0 R.sub.2 is H, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl, C.sub.1 -C.sub.4 haloalkyl, CO.sub.2 R.sub.6, YR.sub.5, NO.sub.2 or CONR.sub.7 R.sub.8 ; PA0 R.sub.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, halogen or alkoxyalkyl of at most 4 carbon atoms; and PA0 R.sub.4 is C.sub.1 -C.sub.4 haloalkoxy or C.sub.1 -C.sub.4 haloalkylthio. PA0 R.sub.2 is H, F, Cl, Br, NO.sub.2, CF.sub.3, NR.sub.20 R.sub.21, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy or S(O).sub.m --C.sub.1 -C.sub.4 alkyl; PA0 R.sub.3 is H, F, Cl, Br, NH.sub.2, NO.sub.2 or OCH.sub.3 ; PA0 R.sub.6 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.5 alkenyloxy, C.sub.3 -C.sub.5 alkynyloxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.5 alkylthio, phenoxy, benzyloxy, NR.sub.10 R.sub.11 or C.sub.1 -C.sub.5 alkoxy which is unsubstituted or substituted by 1-3 halogen atoms or C.sub.1 -C.sub.3 alkoxy; PA0 R.sub.18 is hydrogen, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy; PA0 m is 0, 1 or 2; and PA0 Y is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, C.sub.2 -C.sub.3 alkoxyalkyl, C.sub.1 -C.sub.3 alkylthio, halogen or NR.sub.16 R.sub.17. PA0 R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl or C.sub.1 -C.sub.4 alkylsulfonyl; and PA0 R.sub.3 and R.sub.4, independently of one another, are each hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.1 -C.sub.4 alkoxy or NR.sub.12 R.sub.13. PA0 R.sub.1 is hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, YR.sub.14, CONR.sub.12 R.sub.13, NR.sub.12 R.sub.13, SONR.sub.15 R.sub.16, OSO.sub.2 R.sub.17 or COR.sub.18 ; PA0 R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl or C.sub.1 -C.sub.4 alkylsulfonyl; PA0 R.sub.3 and R.sub.4, independently of one another, are each hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, C.sub.2 -C.sub.5 alkoxyalkyl or NR.sub.19 R.sub.20 ; PA0 R.sub.9 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl or C.sub.1 -C.sub.4 alkylsulfonyl; PA0 R.sub.10 is hydrogen, halogen or methyl; PA0 R.sub.11 is a radical COR.sub.24 or a C.sub.1 -C.sub.4 alkyl group that is mono- or polysubstituted by substituents selected from the group: cyano, nitro, hydroxyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, etc. PA0 R.sub.18 is H, C.sub.1 -C.sub.4 alkoxy and various other organic radicals. PA0 R.sub.2 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, each unsubstituted or substituted by 1 to 3 halogen atoms; PA0 R.sub.3 is halogen, H, NR.sub.4 R.sub.5, C.sub.1 -C.sub.3 alkyl, unsubstituted or substituted by 1 to 3 halogen atoms ro C.sub.1 -C.sub.4 alkoxy, or is C.sub.1 -C.sub.3 alkoxy, unsubstituted or substituted by methoxy, ethoxy, or 1 or 3 halogen atoms; PA0 A is C.sub.1 -C.sub.4 alkylene or C.sub.2 -C.sub.4 alkenylene, each unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl; PA0 E is N or CH; PA0 X is oxygen, sulfur, SO or SO.sub.2 ; and PA0 Q is, in part, OH, CN, NR.sub.6 R.sub.7, SO.sub.2 R.sub.8, cycloalkyl or COCH.sub.1 -C.sub.6 alkyl. PA0 m is 1 or 2; PA0 E is CH or N; PA0 Z is oxygen or sulfur, PA0 R is, in part, H, C.sub.1 -C.sub.9 alkyl or C.sub.1 -C.sub.9 haloalkyl; PA0 R.sub.1 is H, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl or YR.sub.5 ; PA0 R.sub.2 is H, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl, C.sub.1 -C.sub.4 haloalkyl, YR.sub.5, CO.sub.2 R.sub.6, NO.sub.2 or CONR.sub.7 R.sub.8 ; PA0 R.sub.3 and R.sub.4, each independently of the other, are H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, NR.sub.9 R.sub.10 or OCH.sub.2 CH.sub.2 NR.sub.9 R.sub.10. PA0 R.sub.1 is C.sub.1 -C.sub.3 alkyl, C.sub.3 -C.sub.4 alkoxylalkyl, C.sub.2 -C.sub.4 haloalkyl, C.sub.3 -C.sub.4 alkenyl or C.sub.3 -C.sub.4 alkynyl; PA0 R.sub.2 is C.sub.1 -C.sub.3 alkyl, cyclopropyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, allyloxy, allylthio, allysulfinyl, allylsulfonyl, propargyloxy, propargylthio, propargylsulfinyl, propargylsulfonyl, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 alkyl substituted with 1-3 atoms of F or Cl, C.sub.1 -C.sub.2 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 .varies.C.sub.2 alkylthio, C.sub.1 -C.sub.2 haloalkylthio, C.sub.1 -C.sub.2 alkylsulfinyl, C.sub.1 -C.sub.2 haloalkylsufinyl, C.sub.1 -C.sub.2 alkylsulfonyl, C.sub.1 -C.sub.2 haloalkylsulfonyl, OH or OC(O)C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy substituted with C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 haloalkylthio, C.sub.1 -C.sub.2 alkylsulfinyl, C.sub.1 -C.sub.2 haloalkylsulfinyl, C.sub.1 -C.sub.2 alkylsulfonyl, C.sub.1 -C.sub.2 haloalkylsulfonyl or CN, OCH.sub.2 CH.sub.2 NH.sub.2, OCH.sub.2 CH.sub.2 NHCH.sub.3, OCH.sub.2 CH.sub.2 N(CH.sub.3).sub.2, C.sub.1 -C.sub.2 alkylthio substituted by C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 haloalkylthio or CN, C.sub.1 -C.sub.3 haloalkylthio, C.sub.1 -C.sub.3 haloalkylsulfinyl, C.sub.1 -C.sub.3 haloalkylsulfonyl, C.sub.2 -C.sub.3 alkenyl, C.tbd.CH, NR.sub.b R.sub.c or OC(O)C.sub.1 -C.sub.2 alkyl; PA0 R.sub.b is H or C.sub.1 -C.sub.2 alkyl; PA0 R.sub.c is C.sub.1 -C.sub.2 alkyl or C.sub.1 -C.sub.2 haloalkyl; PA0 Y is CH.sub.3, OCH.sub.3 or OCF.sub.2 H; and PA0 R is H; PA0 R.sub.1 is C.sub.1 -C.sub.2 alkyl; PA0 R.sub.2 is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, CF.sub.3 or OCF.sub.2 H; and PA0 Y is CH.sub.3 or OCH.sub.3.
South African patent application No. 81/4874 discloses herbicidal sulfonamides of formula ##STR2## wherein A is a C.sub.1 -C.sub.6 alkyl radical which is substituted by halogen or various other organic substituents or a C.sub.2 -C.sub.6 alkenyl radical which is substituted or unsubstituted;
South African patent application No. 82/5042 discloses herbicidal sulfonamides of formula ##STR3## wherein A is C.sub.3 -C.sub.6 alkynyl;
South African patent application No. 82/5671 discloses herbicidal sulfonamides of formulas ##STR4## wherein A is a C.sub.1 -C.sub.6 alkyl radical or a C.sub.2 -C.sub.6 alkenyl radical which is substituted by halogen or various other organic substituents;
South African patent application No. 83/0127 discloses herbicidal sulfonamides of formula ##STR5## wherein R.sub.1 is hydrogen, halogen, cyano, nitro, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, COR.sub.6, NR.sub.7 R.sub.8, S(O).sub.m --C.sub.1 -C.sub.4 alkyl or SO.sub.2 R.sub.9 ;
South African patent application No. 84/2245 discloses herbicidal sulfonamides of formula ##STR6## wherein A is C.sub.1 -C.sub.6 haloalkyl;
R.sub.1 is hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, COR.sub.6, NR.sub.7 R.sub.8, CONR.sub.9 R.sub.10 or SO.sub.2 NR.sub.11 R.sub.12 ; PA1 m is 0 or 1;
South African patent application No. 84/2722 discloses herbicidal benzenesulfonamides of formula ##STR7## wherein A is a radical of the formula CR.sub.6 R.sub.7 XR.sub.8, CR.sub.9 R.sub.10 R.sub.11 or CHR.sub.7 SCQR.sub.21 ;
South African patent application No. 83/0041 discloses herbicidal benzenesulfonamides of formula ##STR8## wherein R.sub.1 is H, halogen, NO.sub.2, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.5 alkenyl or C.sub.1 -C.sub.4 alkoxycarbonyl;
South African patent application No. 83/3779 discloses herbicidal benzenesulfonamides of formula ##STR9## wherein A is C.tbd.CR;
There is however a continuing need to find herbicides that are more effective and more selective toward agricultural products.